


Out in the Street

by Goose_smoothie81



Category: Supernatural
Genre: Abuse, Alternate Universe, Angst, Angst with a Happy Ending, Dean's a fashionista, Detective Castiel (Supernatural), Fluff, Gangs, Hurt/Comfort, John Winchester's A+ Parenting, M/M, Slow Burn, Street Racer Dean, Street Racing, Tags to be updated with story
Language: English
Status: In-Progress
Published: 2020-07-12
Updated: 2020-07-25
Packaged: 2021-03-04 22:21:24
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 17,174
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25213846
Author URL: https://archiveofourown.org/users/Goose_smoothie81/pseuds/Goose_smoothie81
Summary: When on the road, adrenaline eagerly pumping through veins and lights flashing dizzyingly by eyes, you needed to be fully engaged or not at all, as anything in between would cost you more than just the prize.1995 Chicago. Dean is a street racer turned CI for detective Novak in exchange for a fresh start. The catch? Help the detective take down one of the cities most prominent gangs and not die in the process.He never planned to fall in love either.
Relationships: Castiel/Dean Winchester
Comments: 6
Kudos: 12





	1. Fuel

**Author's Note:**

> My beta is grammarly so please forgive any mistakes they're all mine :)  
> Also new here. Blame the quarantine.

There was nothing as powerful as feeling the hum of a V8 engine vibrating underhand. It was an electric feeling that caused the hairs all over one’s body to stand on end, stimulated, heart fluttering in exhilaration. Anticipation simmered hungrily under the hood of the ’89 Chevy Corvette ZR-1 as she waited on the starting line at Hell’s, her driver, Dean, drumming his fingers on the steering wheel absently as he stared out over Lake Michigan. She was a beautiful car, the Corvette, a dark sleek silver that shone under the street lights, complete with custom specs and skid-resistant tires all done by Dean himself. However, she still didn’t compare to his pride and joy, Baby, his ’67 Chevy Impala. But Baby wasn’t for racing. Baby was too good for that.

Finally, their opponent rolled to a stop beside them, engine rumbling menacingly in a low thrum that resounded in Dean’s chest. He glanced over at the cherry red Ferrari and almost rolled his eyes when he saw that it was a 512BB. The tinted glass of the driver’s window rolled down to reveal one Meg Masters seated behind the wheel, adorned in a red leather jacket and sliding her eyes over Dean and his ride with a sly smile.

“Cute car, Winchester.” She commented, her words dripping with sarcasm. The mischievous gleam in her eye and her close-cropped blonde hair made her look somewhat like a pixie.

“Meg!” Dean greeted with mock enthusiasm. She was in fact one of his least favourite people in the world. “Would’ve figured the Testarossa to be more your style.”

Meg raised one perfectly arched eyebrow. “The BB’s faster.” She replied matter-of-factly with a voice smooth like caramel.

“We’ll see about that.” He smirked and turned back to face the road, the Corvette purring eagerly beneath him. Onto the road before the two cars strode a pair of long legs in black boots and a leather jacket that belonged to Jo Harvelle. Jo spun to face them, bandana in hand and blonde curls bouncing as she regarded the competitors with a girlish smile and a dangerous glint in her eye. She may be a pretty petit but Dean knew that the (somewhat) sweet seeming exterior hid a fierce interior, one full of determination, passion, and an absolutely terrifying temper.

Slowly, Jo raised the bandana in a wide ark until it hung above her head, milking the moment as the two revved their engines impatiently. Dean could’ve sworn that he saw her roll her eyes at the competitive flaunt. In that moment world narrowed down to red and time froze, waiting for the piece of fluttering fabric and the Ferrari beside him to make a move and break the spell.

Suddenly the bandana came down in a flash of crimson and the two machines took off in a deafening roar either side of the blonde. She spun to watch them go, the unmistakable scent of burnt rubber and gasoline saturating the cool night air.

Immediately, the Corvette took the lead from the BB, the Chevy’s lighter body able to go from 0 to 60 quicker than the Ferrari. She flew over the asphalt, but Dean wasn’t able to leave Meg in the dust just yet, as after a few seconds the Ferrari’s powerful engine kicked in and managed to match its opponent's speed. The first turn came and Dean shifted gears, slowing before taking the turn widely. The Corvette drifted, a little more than Dean wanted, but that was expected of the lighter car and he was able to plan for it. Quickly, Dean took control of their spin, changing gear again and speeding off, only fishtailing a little. The Ferrari had less of an issue and was able to gain ground on the Corvette as Meg cleared the corner, hugging in tighter than Dean was able to. A glance in the rear-view mirror confirmed that she was hot on his tail and he floored it, the exhaust ripping in glee as the car sped down the stretch of road, uninterrupted.

The city lights streaked down the Corvette as she passed under the towering metal poles. The second turn came and Dean took it the same, but this time daring to change the point of entry and his angle, in an attempt to coerce Meg into slowing lest she wish to crash into the other car. He drifted almost sideways through the turn and into the street, but his opponent didn’t slow, and for a moment Dean believed that Meg was honest to God going to plough right into him. But instead she aimed for the far side of the road and charged ahead, choosing to box Dean in and forcing him to back off lest _he_ wished to crash into _her_. 

Dean would’ve appreciated the smooth manoeuvre more if he weren’t the one on the receiving end. He growled and he violently shifted gears, frustrated at finding himself blocked in by the bright red hunk. The road began to curve and slowly tighten, inviting Dean to play essentially a giant game of chicken with the larger car before him. Hand on the stick he shifted, riding the sweet spot between gears as the Corvette drifted smoothly over the contour, sitting in the BB’s blind spot. One sharp turn or jerk of the wheel from Meg and he’d be done for. But he took the risk, prematurely shifting back into a lower gear and accelerating before the bend straightened out. He shifted once again. The Chevy whined as they wove around Meg, coming close to clipping the outer curb but breaking free from out behind her vehicle. Risky move upon risky move but it paid off, and the Corvette hurtled past the Ferrari with a roar whilst the latter was still completing the transition.

A few more turns and they would be back at the starting point. It was only a single-lap short circuit tonight but Dean could swing it. Besides, he wasn’t actually here tonight to race; he came to keep Jo out of trouble.

Having learnt his lesson from before, Dean played the following turns safely and took advantage of the open stretches of road to gain ground. Meg remained close by the entire race, but by the time the two reached the final stretch, it was over. If she hadn’t taken the lead by now she didn’t have a hope of recovering it, as the last length of road essentially boiled down to a good old-fashioned drag race and both knew that here, the Corvette would reign supreme. Dean shifted gear and floored the acceleration and left Meg behind in the trial of exhaust, crossing over the line with well over a second between them and a joyful cry.

He slowed and spun the Corvette tightly in a screeching circle, marking the asphalt as he directed to drive back to base, careful to stay out of his opponent’s path. The scent of gasoline and rubber permeated the car as he rolled down his window, cool air rushing in to caress his face. He patted the steering wheel fondly. “We did it, girl.” The driver smiled softly.

The Ferrari cruised towards Dean, pulling up alongside the Chevy driver-to-driver. The window already down, framing Meg’s pouty face as she regarded him coolly.

“Gotta hand it to you, Winchester, that was smooth.” She cooed in her dulcet tones. “Guess you’re gonna be wanting a big prize for beating one of Hell’s finest. Just your luck that I have just the thing to help pass the time real nicely.” She smiled loftily, but the tightened lines around her mouth betrayed her displeasure. Dean parted his lips and looked at her from under his lashes, making a show of gazing at her hungrily.

“Oh, not in a million years, sweetie.” He sang with a smirk and drove off. _Just the thing?_ Was she offering him drugs or sex? It wasn’t uncommon; illegal activities never seemed to have the same defined lines that maybe a club or a school band would have, and it was known that amongst them milled other temptations. But to Dean, nothing about the circus was appealing.

He pulled the Corvette to a stop near the end of the parking lot and twisted the keys in the ignition, the hum diminishing gently underneath him as the engine died down. He had barely shut the door behind him before he was ambushed by a tiny blonde rocket who sprung on him eagerly. Dean caught Jo in his arms and she clung to him, squealing in excitement as he spun the two around gleefully. He used to do the same with Sammy when he was smaller.

“Woah there, Jo! Quit acting like I ain’t the one normally winning!” Dean laughed. He set her down with a playful ruffle of her hair and she batted him away with a glare.

“No, idiot. You won against _Meg_ , in the _512BB_. That’s a pretty big deal Dean.” She stared the taller man down with a scowl, which the latter found quite endearing. She was basically his little sister. Dean waggled his eyebrows and leant in conspiratorially.

“Sounds like that’s a pretty big prize, Jo.” With that money he could finally buy Sam a laptop, maybe even a few of those fancy law textbooks he likes so that he doesn’t have to keep borrowing them from the library each week. A smile spread across Jo’s face.

“Look at that, Azazel doesn’t seem too pleased.”

Dean lifted his head to scan across the parking lot and found the Demons gathered near the cherry red Ferrari several feet away from where Dean and Jo were situated. Sure enough, there stood Azazel Aberdeen, currently chiding Meg who stood arms crossed and mouth twisted like a stubborn child. Azazel was the current king of Hell’s, which is to say champion. He didn’t own the place nor run it, but having that type of status allowed him certain luxuries that others didn’t have. So it was fair to say that having one of his own members of the Demons and long-time champion lose to a drifter like Dean didn’t necessarily reflect on himself too well. But Dean had a reputation amongst Hell’s patrons, and with that extra piece of context in mind, he was sure that the consequences for Masters wouldn’t be anywhere near severe.

The loudspeakers activated with a whine and the tinny voice announced the next racers, echoing hollowly across the enormous lot.

“He’ll get over it.” Dean decided. Azazel glanced over to look at Dean momentarily, his strange yellow eyes glowing in the lamplight and lingering just long enough to unnerve the young man, before turning back to Meg. Dean swallowed.

“Whad’ya say we go cash out then head home?” He slung his arm over the shorter girl’s shoulders and directed her over the asphalt towards the old rusty pavilion near the water’s edge. It served as Hell’s base of operations. They entered the crowd. It was a busy night, and surprisingly warm for autumn in Chicago, but still not quite warm enough to justify the lengths of skin some of the women were showing. Dean couldn’t help but stare a little, thinking to himself that a good pair of jeans with a lowcut top would be just as effective at highlighting their already beautiful bodies without the pain of the chilly night air. Jo drove a sharp elbow into his side, _hard_. She was exhibit A of the good-jeans initiative.

“Quit staring.” She barked. “And why do you want to go so soon? We’re barely halfway through the night.”

They dodged through the masses, distractedly responding to the odd greeting that came from a face in the crowd here and there.

“I didn’t win tonight just so I could go home and have your mom murder me.” Dean reasoned, gently reminding her of the mildly unauthorised nature of their outing. Jo snorted. She couldn’t argue with that. The clamorous thunder of two engines blasting off from the starting line resounded behind him, and both turned to momentarily watch a Lotus and a Lamborghini shoot off into the night. The Lamborghini would win that one, easy.

Stepping up to the pavilion, Dean untangled his arm from Jo’s shoulders and placed it protectively on her back instead. He searched through the heads and noted the absence of one unmistakable mullet.

“No Ash tonight?” He queried. Jo shrugged.

“Think he has a date or something.”

Dean frowned as he processed the words. “With who?”

“Pamela.”

Dean’s expression smoothed out and he nodded to himself. If anyone would be able to handle Ash, it would be Pamela, and vice-versa. Dean picked his way through the people gathered under the canopy, Jo in tow, and came to a stop before the bookie’s desk, which tonight was occupied by-

“Crowley.” Dean greeted.

“Winchester. Harvelle.” The Scottish man returned, addressing the two and matching the former’s flat tone in his own soft, raspy voice. Crowley was a stout man who dressed almost exclusively in black and had round eyes that gave him the appearance of an owl. If owls had more conniving features, that is. He ran Hell’s and took care of the Demon’s finances, but despite this didn’t truly seem to be a part of their gang. No one knew quite what to make of the man, but Crowley sure knew business and Hell’s was one hell of a success for an illegal street racing operation.

“When are we going to have the pleasure of seeing you on the track?” He directed at Jo, who beamed with a criminal smile.

“Soon.” She affirmed and Crowley let out a satisfied grunt.

“Look forward to it.” He stated. “Now, what can I do for you?” The Scot looked between them expectantly, eyebrows slightly raised.

Shoving his hands in his jacket pockets, Dean met that stare head-on. “Wanting to cash in for the night.”

“Ah.” The shorter man’s head twisted as he regarded the taller man, expressionless. “Leaving so soon, are we? The night is young, there’s still time to gamble away all your winnings.”

“You handle the books, when have you ever seen my name next to a bet?” Dean responded gruffly to which Crowley made a face.

“Never too late to start.” He muttered. Licking his thumb, he carded through the giant book laying before, finally landing on a page as Dean shifted uncomfortably.  
“For the two races tonight?” He confirmed. The taller man nodded and Crowley traced the winnings with a finger before he stilled. His eyebrows shot to his hairline. “That’s quite a sum.” He said simply.

Dean and Jo looked at each other, the former with a face of disbelief and the latter with a wide toothy grin, both struggling to contain their excitement. Dean’s mouth opened and closed as he worked to get the words out.

“H-How much?”

“Just over two grand.”

_Holy. Fuck._

“Two grand?” Dean repeated dumbly. He could feel Jo vibrating at his side. Two grand? A driver usually walked away two hundred richer from a victory at most but Dean supposed that this was the reward for beating one of the unbeatable. That was _definitely_ enough for the laptop, and would make a fair contribution to Sam’s college fund. Dean barely registered as Crowley took out a bunch of jangling keys from his pocket and used them to open the bottom drawer of the filing cabinet that sat beneath the desk. Under the harsh white pavilion lights, the Scot pulled out a cashier tray and began to count out bills on the desk between them, all whilst Dean stared down at the proceedings, incredulous, and not really seeing it.

“Will you buy me that dress now?” Jo teased, half joking and half dead-serious. Shaking out his shock, Dean turned to her.

“ _After_ I buy Sammy all his books, then we’ll see.”

Jo nudged him fondly. She knew that Dean wouldn’t be able to resist. Besides, that dress really did look good on her and was modest enough that both he and Ellen would have no complaints about it.

Wordlessly, Crowley placed the money in an envelope and passed it over to Dean.

“There you go. And uh, drive safely.” He added with a sarcastic smile.

Dean uttered a ‘thanks’ and turned to leave. He tucked the envelope deep into the inner pocket of his jacket as Jo led them back out into the cool air, the two of them glancing around furtively for any sign of trouble. As soon as they stepped out into the fresh breeze, he ruffled her hair affectionately.

“C’mon, let’s get you home before your mom has my head for breakfast.”

...

Luckily, Ellen Harvelle had already eaten by the time Dean arrives at the Harvelle-Singer residence. The two are sitting in the living room, separated by the coffee table and about three metres of not enough distance whilst Dean waited for Sam to hurry his ass. He had come to collect his brother so that he could take him to pick up some supplies plus his extracurricular stuff, and ever since arriving that morning had found himself under the extreme scrutiny from the woman. Ellen’s gaze followed him around fixedly, suggesting that she was suspicious of his and Jo’s little excursion and did not approve in the slightest. With narrowed eyes, she stared Dean down over the rim of her mug of coffee and sipped from it. Dean swallowed thickly. It was terrifying.

“Did you guys have fun last night?” She asked, and Dean got a distinct impression that is was a trap.

“Yeah,” His voice cracked. He cleared his throat. “Yeah, we, went and saw a movie.” The momentum of his sentence noticeably picked up about halfway and Dean tried not to wince at his own clumsiness.

Ellen raised an eyebrow. “Oh yeah?” She challenged. “What did you see?”

The boy hesitated. “Seven.”

“Seven?” She replied. “They say it’s quite good.”

There was a thumping on the staircase behind him that could only indicate the arrival of Sam Winchester. Dean jumped up, relieved to see his brother and started ushering him outside as soon as his feet hit the landing, even before he had the chance to say ‘good morning’ to either of the room’s occupants. Dean turned to Ellen whilst he pushed over six feet of gangly limbs towards the door.

“Yeah it’s quite good, Jo will give you all the details.”

Sam looked between them, brow furrowed in confusion but not overly surprised by his brother’s strange antics. He’s had years to get used to them.

“Morning Ellen.” He greeted as the door swung dangerously close to his face.

Ellen smiled warmly. “Morning Sam.”

Dean disappeared through the entrance, pulling Sam out after him before quickly popping his head inside to call out. “Bye Ellen!”

“Bye boys!” She called back, her amused snort following them outside as Dean shut the door with a sigh.

Sam looked at his brother.

“What the hell was that, Dean?”

The older boy paused at looked at Sam, breathing heavily as the adrenaline left his body. A moment passed before he huffed. “Get in the damn car, Sammy.” Sam chuckled to himself and went to go do as told.

Dean went all out. He started their day with lunch at one of Sam’s favourite haunts, and then took him all around the city chasing after books, shoes, and finally, a laptop. He could tell that Sam was instantly suspicious of the day right from the beginning, but his little brother didn’t say a word throughout the entire trip, allowing himself to be pulled along by Dean who was giddy like a kid on Christmas. He couldn’t help it, it felt like Christmas. Better than even, and Dean was lavishing in the opportunity to provide for his kid brother as he deserved. Just as he’d been trying to do their entire lives.

The back seat now stacked with books and the front with two sated boys, Dean drove them back to Willow Springs, travelling in an easy silence with nothing but The Rolling Stones and the comforting hum of Baby’s engine between them. Sam looked out the passenger window, watching the buildings and trees blend and merge as they drove through the Chicago suburbs, the hazy afternoon light catching his messy chestnut hair at just the right angle to give it an auburn gleam. Glancing over at his little brother, Dean was all of a sudden hit with a deep sense of nostalgia, of those days and nights in which the two would take to the road and just _drive_. Whether it was to escape the house when their father was in one of his moods, blow off steam after an argument, or just to talk, the two would jump in the Impala and go. Sometimes to the seaside, sometimes to one of the preserves, even a couple times to the prairie. And sometimes they just remained on the road. Aimlessly cruising over the asphalt as Dean steered off any anger, any terror, any grief until the ugly feeling was buried once again and he felt in control.

And he was reminded of one specific memory, of driving through the golden light of the late autumn afternoon, the roads flanked either side with trees in varying shades of green to yellow to orange to red and even to purple, a kaleidoscope of colours brought to life by the sun’s rays. And of looking over at Sam, who was fourteen at the time, staring out the window at the world placidly as they drove through it, a youth expecting so much from it all, the sun catching the auburn tones in his hair just as it was doing now.

In the present, Sam turned his head to face Dean, catching the stray lines of wistfulness that remained on his brothers face and smiling at him in response. Riding off the ruminations of a younger Sam, Dean was struck by that smile; struck by not just the tangible change but also the intangible. By the light that shone in his warm brown eyes which were now free of the tight lines that once bound them, by the dimples that moved carefree with his unbridled laughter, by the soft yet confident manner in which he moved, no longer careful and unsure, restrained, like he used to be barely a year ago. His little brother was on the cusp of adulthood, done waiting and ready to go seize what life had to offer and Dean reflected with a sense of sorrow that being kicked from their house was most likely the best thing that had happened to Sam. Now he was free, still with burden but now with choice, and a future within his grasp.

Dean smiled back, but it felt weak.

“Still hoping to get to Stanford, Sammy?” The words floated softly in the air. “Gonna be the one to defend my sorry ass when I eventually get caught?” He teased, glancing over with a playful look on his face.

Sam scoffed. “You know if you want to support my career there are better ways to do so.”

Dean snorted. “Bitch.”

“Jerk.” A moment passed before Sam spoke again. “Yeah, I’m still hoping. Next year when entry comes ‘round I’ll be ready.”

“Don’t doubt it. _And_ ,” Dean gestured with his finger. “You’ll have a year’s worth of all that extra study to get a leg up on. And you know what? I’ll drive you over to California myself. We can make a trip of it, just you and me and the road.” _Like it’s always been_. The words got caught on his lips.

Sam sat back in the passenger seat. “You, me, and the road.” He repeated softly, gazing out the window serenely. That gaze moved to Dean. “I’m not going to leave you, Dean. We’ll keep in contact, I’ll be back for the holidays, and you’ll come to visit.”

“I know.” Dean replied, not believing it but believing that those were the words Sam wanted to hear. But the expression elicited from Dean’s response suggested that his little brother saw right through him.

“You could come with me, you know.”

Dean almost swerved in shock. He glanced over at the other boy who was looking at him earnestly. Move to California with Sammy. Hell, the number of times Dean had fantasied about doing just that.

“Naw, Sammy, I couldn’t cramp your style.” He laughed, trying to play off the intense eagerness that the idea filled him with. “And besides, can’t just leave dad.” He added quietly.

“Dad’s an adult. He can take care of himself.” Dean caught the hidden sentiment behind the words. _Dad’s not your responsibility._ The older boy scowled.

“He’s family.” He stated, leaving no room for discussion.

Sam looked at him tightly but remained silent. They both knew how this argument would end if they were to dive into the subject.

“Well, you’re always welcome.” Sam affirmed in his own ‘no room for discussion’ tone.

Dean’s expression softened. Even when irritated his younger brother was still aggressively kind-hearted. Dean silently thanked the world for not taking that away from him.

“Thanks, Sammy.”

...

After another monotonous week of work, beer, cars, and coffee, Dean found himself back at Hell’s after a particularly bad incident with John Winchester. He just needed to get away from the house and immerse himself is something exciting for a while, a distraction, and street racing would serve that purpose perfectly. When on the road, adrenaline eagerly pumping through veins and lights flashing dizzyingly by eyes, you needed to be fully engaged or not at all, as anything in between would cost you more than just the prize.

And that was how Dean found his escape. Do or die. He passed the majority of the evening blissfully absorbed. It was easy to lose himself within the cool lakeside air of East Chicago, currently filled with the scents of rubber and gasoline and cheap whiskey, the harmonies of cars speeding past and choirs of people cheering, and the powerful vibrations of engines that rumbled through the asphalt and settled deep in Dean’s bones, filling him keenly with anticipation. An engrossing feast for the senses, and the perfect distraction for a lost man.

The young man threw himself into a couple of races, signing himself up to challenge against a few faceless names (no Demons this time), defined only by the cars they drove. He beat each of them, and after the third, resigned himself to watching a few events, perched on the hood of his Corvette and wrapped in his leather jacket with a bottle of beer in hand, before turning in for his winnings and taking off for the night.

And he was at the point of doing so when distant sirens sounded and the unmistakable red and blue lights of police cars began flashing in the corner of his eye.

His first instinct was to take off, fly through the darkened streets of East Chicago, but a nagging feeling in the back of his head warned him against it. If it were some organised sting, there would be traps set all across the escape routes, waiting to ensnare those who made a desperate break for it just as he were about to. Just as many were currently doing.

The crowds of people scattered frantically, heading towards cars or the pavilion or to jump the fences across the large lot. Dean swore he saw a few jumped into the lake. One by one, engines fired up in explosions of sound which only served to add to the already chaotic atmosphere. Dean slid off the hood of the Chevy and swung into the driver’s seat. He was going to wait until the last possible moment before making his break.

Police cars filed in from Hell’s entry points, punching through the clouds of smoke and exhaust that now billowed across the grounds, each coming to a screeching halt all across the lot as people scrambled out of their way. Dean revved the Chevy’s engine, watching for an opening in the blue and red haze. He spotted one and took off in a puff of mist, weaving through the oncoming police who froze or swerved out of surprise of finding the Corvette headed straight toward them. Dean shot out onto the streets of East Chicago. Now, he just had to hope that the awaiting traps were already occupied with prey.

The world narrowed down to the one goal of escape, and almost methodically Dean made his way through the turbulence, dodging cars, people, and pitfalls as police cars raced hotly on his trail. Exhaust fogged his vision and blurred the red and blue police lights which only served to further blind him. It was pandemonium, the air filled with the roars of engines and squealing tires and people shouting in all directions. He was shifting gears almost as fast as he was driving, needing to make quick turns or reverse out of barricades in a hurry, and finally came to his own demise when upon being followed into another darkened street found it blocked off by two heavy vehicles.

“ _Shit!_ ” He swore, swinging his head around to find his only exit filled with flashing lights. Officers piled out of the cars as smoke came from the street behind to engulf them, brandishing guns threateningly and shouting commands over the chaos.

“Step out of the vehicle!” “Hands in the air!” “Out of the car now!”

Seeing no other alternative, Dean switched off the Chevy’s engine and slowly exited the vehicle and within seconds of stepping onto the road was tackled roughly down by overzealous cops. Head meeting the freezing asphalt heavily, Dean hissed as his face grated against the ground and his hands were wrenched behind his back and cuffed tightly, the multitude of voices above him clashing in his ears. They were probably recounting his rights to him.

Before he knew it, Dean was being yanked up to his feet and led to one of the vans that had blocked off the street, where the officers threw him in to join several other faces that already occupied the space. They all stared blankly at differencing points, some watching the proceedings of the night through the tiny windows, some sparing glances at Dean, others just sitting, resigned. Awkwardly, Dean stumbled onto a bench beside a haggard-looking woman and laughed bitterly to himself. He didn’t mean to follow through with his little joke to Sam.

After roughly thirty minutes of waiting in the tense atmosphere, the police piled back into their vehicles and drove them to a nearby precinct, whereupon arriving each detainee were unloaded, stripped of their belongings, and filed into dim, cold holding cells. Some yelled out in angry protest, speaking profanities at the officers who continued on, unphased, and others tried to strike up stilted conversation with their newfound roommates. But thankfully no one in Dean’s cell was feeling in a particularly chatty mood. Dean certainly wasn’t, he was too far trapped on his own head, sullenly hunched in the corner with a surly look on his face as he anxiously worried about the future, about what was going to happen next, about what was going to happen to Sam, to his dad, to Bobby and Ellen and Jo. After the initial pain and suffering he was about to put them through, the young man figured that in the long run, they’d all be better off without him anyway, a realisation that brought a fresh wave of agony to his already wrecked mental state.

Throughout the duration of the night, cops came and went, chatting between themselves, passing around files, sometimes taking people from their cells. Dean noticed a distinct lack of Demon members amongst the detainees, in fact, he couldn’t recall seeing many down at Hell’s earlier that evening. He supposed that maybe it was a blessing in disguise, as if the cops were to find a shred of gang-related evidence at Hell’s, they would certainly shut down the racing operation for good.

Finally, an officer came for him. He pointed to the boy, declaring ‘you’ ominously and did not direct another word to the boy for the remainder of the night. Dean allowed himself to be led through the dirty blue hallways and under the cold fluorescent light of the precinct, and into a dingy interrogation room where he was left, alone. He seated himself at the cold metal table after the officer had shut the door behind him. It was too bright and all of a sudden too quiet. Dean didn’t know what to do with himself. He actively avoided looking at the giant mirror beside him and instead chose to worry at the skin around his fingernails anxiously. He supposed this was hell.

Despite his expectations, the boy wasn’t left alone for too long. After only a few minutes another man entered the room, and judging by his more casual attire, this was a detective. There was no bravado like the other cops, no need to command dominance over the room, but a self-assuredness that was evident in his movements and the way he carried himself. In one hand sat a couple of manila files, and in the other a steaming cup of hot coffee, and with a strong shove of his elbow, the man shut the door behind him. 

Dean watched him warily as he entered, before averting his gaze as the detective turned and made his way over to the table. He deposited the cup of coffee under the boy’s nose and the he looked up, meeting the other man’s gaze momentarily and forgetting where he was. Those eyes, the detective’s eyes, were a brilliant bright blue, the colour of pristine lake waters that ran deep, a colour so clear yet so dynamic, vivid, that despite the bleak light that threatened to wash all the colour from the room, still shone blazingly. 

Blue eyes pulled out the chair on the opposite side of the table, and Dean was struck by how he chose to lift the chair instead of dragging it, possibly to avoid loudly grinding the legs against the concrete floor. It was such a stupid detail to notice, but it spoke volumes over the type of person he was. The other man settled in, flicking through the case files briefly as Dean watched him intently, not sure what to make of the other before him. He had a sharp nose and full lips and a mop of messy black hair that suggested he’d just crawled out of bed. And he was young, Dean judging that he couldn’t be more than seven years older than himself.

“Dean Winchester.” The detective addressed, placing the files down on the table before him. His voice was gravely and deeper than Dean had expected and held an effortless authority to it. “Street racing, money laundering, tax evasion, and possible gang involvement.” He read from the file, those radiant eyes flicking up to look at Dean. “All with jail time and considerable fines.”

Winchester sat silently as the words hit him, followed by their implications.

“With respect, the street racing and minor,” he pinched his fingers together with a wink “ _minor_ , tax evasion I may, or may not, be guilty of. But I have no clue how to launder money and am definitely not involved with any gang. Sir.” He added as an afterthought, unsure of how to address the nameless man.

The detective eyed him expressionlessly. “Detective Novak.” He supplied. “And I won’t be the one you need to convince of that. However, I will warn you that as it stands, your chances of pleading innocent to any of these charges are rather slim.”

Dean remained silent, staring the detective down who was unphased by the former’s taciturn demeanour. Of course they were. felt as if the walls were beginning to close in.

“I would like to discuss Azazel Aberdeen.” Novak pressed on.

Dean narrowed his eyes. “What about him?”

“One of my CI’s reported that the Demon gang were planning to start expanding their product and push it into new territory across the city. This is of particular interest to us as not only are we trying to remove _sanguine_ from the streets, but if the Demons start encroaching on the north side of the city we fear that they may clash with the Angels and start a gang war.” He didn’t waver as he explained the situation, conveying it all with a straightforwardness that seemed almost clinical.

“And you’re telling me this all this why?” Dean asked gruffly, his eyebrow raised as he regarded the detective suspiciously. The detective cocked his head and his eyes flicked to the table.

“For reasons I cannot disclose to you for your own safety, I am in need of another CI.” His gaze returned. “You are already on Aberdeen’s radar, all you will be required to do is infiltrate the Demons and report to me their plans, shipments, and any other information that could be of use.” With a watchful eye and an impassive face, the detective observed Dean intently, waited for some form of response from the man seated across the table. That response came in the form of Dean’s mouth opening and closing intelligently as he processed the detective’s words. Then he began to laugh, and upon seeing Novak’s stony expression, realised that this was not, in fact, a giant joke. Dean coughed and cleared his throat as he schooled his features, trying to play off the little outburst coolly.

“You’re joking.” He blurted.

The detective cocked his head and his blue eyes narrowed minutely. “Does this _seem_ like a joke to you?”

No. It really didn’t. “With all due respect, Detective Novak. I know you look at me and my kind, and immediately you see ‘criminal’, but I uh, I actually don’t do that stuff. No drugs, no kidnapping, no funny business.” He thumped his chest with both hands. “I-I, I just do what I gotta do to survive.”

The lines on the detective’s face softened somewhat. “I know. That is why I am giving _you_ this chance.” He leant back in his chair and considered Dean evenly. “In return for your cooperation, all charges against you will be dropped and you’ll be free to move on with your life as you wish.”

“And if I choose not to?”

The detective’s mouth twisted downwards as he regarded Dean’s question. “You will take your chances at court, likely serve jail time, and for the rest of your life be defined by that one black spot on your record and not by your integrity.” It was cruel, having his words twisted and thrown back at him in such a direct manner, but the detective could hardly be blamed for speaking the raw truth.

Dean crossed his arms on the table before him, almost as if to protect himself, and absently played with the fabric of his sleeves. Between the two options, neither were favourable. Buried deep in a dark part of Dean’s mind, he thought of prison and he saw an end to it all. In there he would be free of responsibility and a burden to no-one but the system, unable to disappoint anyone as he would have no one to disappoint. It felt, inevitable, in a way, as sooner or later everyone was going to leave him.

But.

He wouldn’t do that to Sammy.

That, he could never, _ever_ , forgive himself for.

So that left him with only the one choice.

With guarded eyes, Dean peered at the detective severely. “If I do this,” he began, voice low and dangerous, “promise me, that no matter what happens, my family will be safe. Promise me, that you will protect them.” Slowly, he crept up and leant over the table and Novak. He snarled. “Cause I swear to you, that if anything does happen to them, if a _single_ hair on any one of ‘em is harmed, you’ll have a lot more than just the Demons to worry about and that I promise you.”

The dark-haired man stood and met Dean face on, leaning over the table to meet his challenge, stopping only a hairsbreadth away from the other’s face. “Are you threatening me, boy?” He breathed.

“Promise me, Novak.” Dean sustained, not backing down.

For a moment the detective glared at him, those deep blue eyes piercing into Dean as they wandering across his face in search of something. Finally, he relented. “I promise.”

Relief washing over him heavily, Dean slowly slid back into his chair as the fight drained from his body. He looked down at the coffee cup whilst in turn, the detective looked down at him, mind churning with the pure insanity of it all. At that moment Dean made a promise to himself; that if he got through all this, survived whatever hell he was going to get himself into, that he would move over to California with Sam.

Novak straightened up and rubbed a hand over his face. “It’s late.” He said to no one in particular. “We shall reconvene another day to discuss the operation in detail. I’ll give you a mobile phone before you leave, keep it hidden and use it only to communicate with me and no one else. And don’t ignore me. I know where you live I _will_ arrest you.”

Dean snorted. “Deal’s a deal.” He said and sighed. “I’m gonna need the Corvette back.”

Novak huffed a small laugh. “I’ll see what I can do.” And flashed a small smile.


	2. Round and Round

**Notes for the Chapter:**

> It's a long one!  
> Uni's back so as much as I'd like to update this semi-regularly we'll just have to see how the semester goes.   
> Updated tags and ratings. Ao3 has ruined me I forgot that 'explicit' also refers to language and not just the juicy stuff so fixed that whoops.  
> Also decided to write in the accents because why not.
> 
> **Triggers for abuse.**

_Novak_

True to his word, Castiel Novak was able to retrieve Winchester’s Chevrolet from impound and returned it to the youth, who beamed brightly upon arriving to the facility to collect it.

“Aww, Honey!” He had cooed, running a hand reverently across the car’s bonnet. “How I missed you!” It would not have surprised the detective if Dean had kissed the vehicle right there.

A few days later they had agreed to meet in a diner in Riverside, _De L’ame_ , owned by Missouri Moseley, a long-time friend and mentor to Castiel. Secrecy was going to be imperative to this whole operation, and the detective knew that he could count on Missouri to keep things under wraps. The last thing he needed was word of his side-operation getting back to the department.

Especially if Castiel was right about his theory.

Castiel settled in on one of the wooden stools that ran across the counter, choosing a spot in the far corner and signalled for a coffee. He quite liked Missouri’s place, it was a touch dimmer than the average diner but lovingly decorated with a mis-match of nice purple wallpapers with gold touches and little potted plants that sat on each table and across the walls. Music wafted across the space, flowing through the air warmly and dancing with the inviting smells of vanilla and cinnamon that drifted from the kitchen. It was different than the usual ‘diner’ but it was Missouri’s, and her down-to-earth aura had attracted a unique and loyal cliental that adored the atmosphere. Castiel included.

Someone slid onto the seat beside him and the detective looked over to find Dean by his side, cheeks flushed from the cold and adorned in the black leather jacket he had quickly come to associate with the boy. He sported a purpling bruise that wrapped over his jawline and lower cheek, and chose to sit between the detective and the wall, hiding the mark from the world.

“Howdy partner.” Dean greeted, flashing the other man a lopsided smile as he waved his fingers for a coffee. Castiel rolled his eyes at the flippancy the words displayed.

“Morning.” He returned somewhat gruffly, taking a sip from the steaming cup before him. A waitress came to fill a mug for Dean, and the detective watched her from the corner of his eye as with a shy smile she lingered after the blonde had thanked her. Those eyes then flicked over to Castiel and she hurried off. Dean snorted into his cup.

“Wow, you really know how to treat the ladies.” He teased, green eyes twinkling as they regarded the other man. Castiel frowned and put down his own mug.

“This is a delicate matter, we can’t risk people listening in on our conversations for their safety and for ours.” 

Dean assented silently with a small bob of his head. “That reminds me,” He began, concern softly pressing in his delicate features. “You couldn’t tell me why you needed a new CI ‘for my own safety’ so why? What happened to the last guy? I wanna know what I’m gettin’ myself into.” The words came out less accusatory than Castiel had expected, but rather more purposeful. He had reason to be concerned the detective reflected, as in their first meeting he had been rather vague with the man sitting across from him.

“Nothing happened to them, they are simply not where I need them to be.” He stated.

The blonde man leant his elbows on the counter before him, turning to glare at the detective flatly. “And you couldn’t just, move them?” He moved his hand to punctuate his point.

Castiel shook his head gently. “It would’ve been too difficult.” 

“Meanin’?” 

_Incredibly complicated, out-of-character of the CI, and a risk to the entire operation in more than just one way._ “Exactly that.”

Dean nodded in response, clearly not wholly satisfied by the response but accepting Castiel’s reasons.

“Also,” he continued. “East Chicago is in Indiana; how did you guys get the jurisdiction to carry out a sting op across the state border?” Castiel was momentarily distracted by the way Dean’s midland drawl languidly rolled across and lengthened the ‘a’s in ‘Indiana’. He drew his lips into a line. This kid was thorough.

“They were searching for somebody, a matter of state security.” His voice was clipped. “I’m not at liberty to discuss the details.”

“Not your case?”

“No.”

“So you were just, hangin’ around the station at two in the mornin’?”

“I,” Castiel hesitated, frowning slightly at the counter, “got a call.” He finished cautiously. He looked at Dean, his annoyance beginning to seep into his tone. “Any more questions?” 

“Yes, the one.” The young man held up a finger and flashed an asinine grin at the detective. “Do I get a gun?” He wiggled his eyebrows and Castiel sighed, pinching the bridge of his nose. 

“No, you will not get a gun.” He groaned.

Dean inclined with his head, and swiping the mug off the counter, assented. “Your loss.” He took a sip. 

Castiel suppressed an eyeroll. He was well aware that the boy was winding him up purposefully, but regardless, he found himself growing frustrated. Seated in the warm diner and surrounded by people blissfully enjoying their Saturday morning, he was forced to consider the possibly that much of that frustration was coming from himself and his own anxieties regarding the case. A heavy sigh escaping through his nose, Castiel attempt to expel some of those pent-up feelings. It would do him no good to ruminate upon something he was unable to change. 

“When you said that I was on Azazel’s radar, what did you mean?” When the question came out of Dean it was hushed, guarded yet intense. Castiel turned to the other man and found him staring forward intently at the plants on the wall. He must have sensed his gaze upon him, as after a moment the boy turned to lock eyes with Castiel and the detective’s breath hitched. The diner’s subdued lighting was favourable on his freckled skin, and some of the coloured bulbs that dotted the wall behind the counter caught the edges of Dean’s hair, softly dusting it lilac and lightening the bruise slightly. He cleared his throat as Dean watched him expectantly.

“Your father,” the detective began gently but trailed off when the blonde spun away as if he were stung. Castiel waited

“He owes them money, doesn’t he?” The boy spoke up. When no answer came he continued. “How much?”

“Fifteen thousand.”

Dean sat sullen for a moment. “That stupid son of a _bitch!_ ” He hissed, smacking the counter before him with a hand. A few heads whipped around to glance in their direction upon hearing the outburst, but none commented on it. They just stared until they were sure the spectacle had ended. Castiel glanced around warily before settling his gaze back on the seething boy beside him. Dean fidgeted where he sat. It was strange to consider that moments ago he had been joking around with the detective and was now glowering something fierce. In an odd sort of way, he reminded Castiel a little bit of a dog; one moment playful and the next barking viciously, energy always directed to one feeling at a time.

“Dean-”

“God, I hoped that he wasn’t dumb enough to do such a stupid thing.” He muttered, turning his head slightly to the look at the counter before Castiel, keeping his body twisted the other way. It was an almost shy gesture, hiding has face away from the detective like that, and from the slither of skin Castiel could see he found Dean’s expression to be dark, unsurprised and bitter. How was someone so young was capable of conjuring such an intricate blend of emotion underpinned with a raw, deep resignation? At a loss of something else to say, Castiel returned to the meeting at hand.

“There is also the fact that you keep beating members of the Demons on the road. Azazel seems to have drawn favour on you due to it.” 

Dean stared intently at the mug in his fingers as he slowing rocked it across the wooden bench.

“Well aint that something.” He scoffed. Softly, the previous song faded from the air and ‘Purple rain’ began to fill the space in the silence.

“So I guess that’s the plan then,” Dean grumbled quietly. “I use my dad’s debt as an excuse to join their gang, work it off with them.”

“Currently it’s the best angle we have.”

“I hate it.” Dean stated with no objection in his tone. He finished off the coffee in his mug, neck bobbing as he swallowed down the last dregs of liquid. 

“But we may have a small problem, concerning the raid at Hell’s last week.” 

Castiel’s eye glided over Dean as he played with the empty coffee cup. 

“No need to worry.” It was a strange sentiment for the detective to express. “As you astutely pointed out before, Hell’s lays in Indiana. Without any priors or evidence that a person’s crimes were committed on this side of the border, we were unable to convict most of the people apprehended. For the purpose of your cover, that also included you. I would wager that in no less than another week, Hell’s will be operating at full capacity again.”

Dean snorted and laughed to himself. “That is one smart son of a bitch.” Admiration coated the words and Castiel needed not to ask to know exactly who he was referring to. They were indeed a cunning and crafty human being.

From the kitchen door at the other side of the room emerged Missouri Moseley. She was donned in her signature magenta and adorned with beaded jewellery, always a bright exterior that didn’t even begin to express her loving and intelligent interior. Upon spotting Castiel, the woman smiled warmly, and headed over to where they sat, swiping a coffee pot off one of her waitresses as they passed by. She stopped before the two boys.

“Always a pleasure to lay eyes upon your sweet face, my little angel.” Missouri greeted in her soft voice, her presence filling the space with a lavender scent. With warm walnut skin and observant wise eyes, Missouri carried a maternal air about her and was not afraid to show some tough love when required. She was the closest thing Castiel has ever had to a mother, and he owed so much of his emotional growth to the gentle and mysterious woman who currently leant against the counter before him.

“Morning Missouri. You’re looking well today.” 

“Why thank you, but I wish I could say the same to you.” Lips pursed, she gave him a pointed look and Castiel winced. For the past couple weeks, he had been working long hours on and off the clock. The bags under his eyes were turning a darker shade of purple and he made less of an effort to groom himself. He was beginning to look a little haggard.

Missouri then turned to Dean and gave him a stern eye. “You.” She examined the boy up and down. “If I give you a refill do you promise to stop disturbin’ my customers?”

Dean blinked dumbly at the woman. “Uh, y-yes ma’am.”

“Good.” She tipped the pot into his mug. “Now, I’m not gonna stick in your hair too long, but I’ve got a fresh pie straight from the oven and I was wonderin’ if you boys would like to try a slice.” She smiled softly at them, and in that moment Castiel realised that Missouri must’ve seen something in Dean to be offering the beat-up boy a slice of her baking with a genuine smile. Dean’s eyes widened at the offer. 

“You already know that I would eat anything that comes from your kitchen a long as it hasn’t touched an apricot.” Castiel responded, smiling sheepishly at the owner. 

“I do. And you, boy?” That last part was directed at Dean, who sat stunned.

“I-I would love a slice. Thank you.”

She beamed at them. “One slice of pie coming right up.” And spun on her heel to bustle away.

Immediately, Dean turned to Castiel. “Her name’s Missouri?"

"Yes."

"That would explain all the Fleetwood Mac.” Dean muttered under his breath.

Missouri returned, this time carrying two steaming plates of golden pastry filled with something purple. She set them down on the wooden counter proudly, and the aromas of cinnamon and nutmeg and something zesty wafted up from the plates before them. Castiel’s mouth watered.

“Spiced plum pie, gentlemen.” She announced, before leaning in with a sly smile and adding. “It’s got a bit of a kick too.” She winked, and straightened to watch them in anticipation.

Picking up the little gold fork from the plate, Castiel sliced into the pie and separated himself a chunk of the sweet-smelling dessert. He brought it to his mouth and. Holy Hell. The buttery crust melted away to reveal a harmony of flavour that exploded on his tongue. A base of sweet plum, spiced evenly with cinnamon and nutmeg and cardamom and aniseed, orange zest punching through in places, laced with notes of brandy which tingled his throat gently as it went down. From the corner of his eye, the detective watched as Dean moaned almost obscenely around a forkful. Missouri chuckled.

“You have outdone yourself.” Castiel expressed. “This, is _incredible_.” 

“Ditto.” Dean muttered through a mouthful.

“Well I’m glad to hear it. Now, I gotta go take care of some things, Saturday mornings you know.” She made a move to leave but spun at the last moment as if suddenly reminded of something critical. “Castiel, don’t forget to touch base with me before you go; there’s a few things we gotta discuss.”

“I will.” He promised and Missouri smiled. 

Dean stared at Castiel as she left, brow furrowed in confusion. “Your name is _Castiel?_ ” He blurted, disbelief coating the words. “That’s _actually_ your name.” 

Castiel drew his lips into a line. “I’m already rather aware how unusual of a name it is.” He stared at the boy flatly. Even after years, the astonishment never ceased to irritate him.

“Does it mean somethin’?” Dean’s voice was muted. 

“I was born on a Thursday, so the nuns at the monastery decided to name me ‘Castiel’, after the angel of Thursday.”

Dean was silent for a moment. “Oh. I’m sorry man I didn’t know.” He genuinely sounded apologetic but there was a marked absence of pity in his tone. Instead, Castiel found empathy in its place, and remembered a note in Dean’s file stating that he had lost his mother in a house fire back in Kansas. “Your life must be some story.”

Castiel exhaled softly. “No need to be sorry.” He smiled weakly at the other man sitting beside him. “And, I suppose it is. But it’s a story for another time.”   
They finished their pie in silence.

_Winchester_

On the edge of Harvey sat a dilapidated and grim looking house. For much of the time the house sat cold and alone, through the windows all was dark and quiet, not a single sign of life emitting from the interior. When the house was occupied, it was occupied by two sombre looking men, one old and one young, one outwardly angry and the other inwardly so. It was difficult to determine whose ire was more insidious. Only when these men were inside the glum shed did the house limp to some semblance of shaky life. A light would be switched on here and there, sometimes the glow of a television screen in a dark room would remain flickering throughout the entirety of the night. Sometimes raised voices could be heard, arguing, their words muffled by the rotting walls but their agitation and grief palpable. These disputes were often accompanied by loud bangs or crashes, strange climatic thuds that sometimes ended the spectacle for the rest of the night. No neighbour commented, no one called no body. To the other residents of Harvey, the Winchester residence was just another troubled house found in the troubled parts of south Chicago. 

It was Friday evening, which mean that John Winchester got off work early. The perks of working in construction. With a week or more to kill before Hell’s was back up and running, Dean found himself simmering uncomfortably in his thoughts, unable to do anything but wait, knowing that these were most likely the last moments of normalcy he was going to have for a while, if not forever. But it was hard to simply live in them. He was struggling to enjoy the time he had, as in the back of his mind the inevitability nagged at him almost 24/7. Even at times when he was blissfully unaware or fully absorbed in something else that reminder would always find a way to wriggle back into his mind. It kept him up at night, made him skittish, and with a strange detachment, he began to make preparations to disappear.

And that is how Dean found himself trying to feebly broach the subject with his dad. It was wiser to poke at a sleeping bear.

On this Friday night, three men were found inside the Winchester residence; the two Winchester men and John’s buddy Jack Daniels. Upon entering the gloomy living room, Dean found his father seated in his usual spot in the dirty armchair, nursing a glass of whiskey and already buzzed, mindlessly watching the TV screen before him. It was too quiet to be audible.

“Dad.” Dean spoke carefully into the still air. John made no motion to indicate that he had heard his son. Dean stalked around the chair until he was standing before the chair, placing himself carefully so that he was not blocking the screen but was still in John’s line of sight. John swung his head to look at Dean.

“What?” He mumbled. Under his father’s eye, Dean stood to attention. He kept his back straight and his head high. He didn’t fidget, as much as he wanted to, but instead made a conscious effort to keep his arms still and at his sides. He took in a deep breath. He had rehearsed his lines rigorously.

“This may sound like it’s comin’ from out of the blue, but somethin’ happened recently that has forced me to do some considerin’, and I need to know that in case somethin’ were to happen to me, that you’d be okay.” Dean spoke into the cool air with an even and measured tone, cautious, but not soft. Wordlessly, John regarded Dean with a heavy brow and the boy wanted to fidget under that gaze. A slow anger seeped into his father’s features and Dean braced himself for the impending storm to come, dread creeping up his throat. 

“Are you suggetin’ to me boy, that you’re gonna _leave_?” Low and weighty, the words tumbled from John’s mouth and Dean had to steel himself in order to stand his ground. He was completely unsurprised that things had gone south this fast. The older man lifted himself in his chair, leaning forward as he spoke so that a slither of the cold light from the kitchen drew a line down his flushed face. “It that was this is? Some bullshit excuse to clear your conscious of abandonin’ your family? Just like your coward brother? Huh?” Fuck, he was drunker than Dean had anticipated.

Suddenly, two distinct pathways became apparent to Dean in that instant. Two potential roads to take, each with endless possibilities. He could respond how he usually would, he could grovel, or at least try to, leave the heavy conversations for later, lie. Even when Dean got riled up, he would force himself to back down again, to retreat, to avoid. Avoid, avoid, _avoid_.

Or.

He could tell it like it was. He didn’t have time anymore to skirt around complicated situations. To dissect them with surgical precision. No, he was gonna charge headfirst into this one and reap the consequences as they may.

“First of all, leave Sammy out of this, this has nothin’ to do with him. Second, I’m twenty-one, dad. In a couple of months, I’ll be twenty-two. At some point you gotta face that I’m not gonna stick around forever, at some stage I’m gonna move on and I won’t be here to take care of you and there’ll be nothin’ you can do about it.”

John was on his feet swiftly and Dean stepped back.

“The fuck you mean by that?” He yelled, eyes wild as he advanced on the youth. “You ungrateful brat! After everything I’ve ever done for you boys, you just gonna walk out on me like that! You too, Dean?”

Dean hated the suggestion hidden beneath his words. You too, Dean? As if Sam had no reason to leave, as if Sam were some selfish child. As if Dean were somehow better than his brother for choosing to stick around waste his life instead of make something from it.

“I’m not walkin’ out on nobody, but you gotta be able to take care of yourself like a fuckin’ adult!” Behind him, the image on the television screen shifted and cast the room into a red haze. 

“Whaddya tryin’ to say by that, huh? That I’m not a capable person? That I can’t, _take care of myself_ , huh?” Suddenly John’s expression twisted into something akin to amusement he and began to laugh, a short bitter noise that came from the old man in breathless bursts. He jabbed a finger in his son’s direction and the amusement fell away as quickly as it came. “That’s rich comin’ from you.” He sneered.

“Comin’ from me?” Dean scoffed. “I’m not the one who can’t hold down a job and wastes all his money gettin’ drunk every night.”

“You watch your mouth, Dean.” John shot back, voice dangerously low. “It’s my money I can spend it how I want.”

“But it’s not even your money, is it dad?” John’s eyes widened minutely and he stared at his son, lip trembling in anger. “Can’t even answer me, huh? Fuckin’ pathetic.”

“You little shit!” John was seeing red now. “Is this the thanks I get for raisin’ your sorry ass? Too hard for you to pay some bills? You think it was _easy_ for me?” _No, clearly it wasn’t._

“Seriously? Do I understand to you expect us to _repay_ you for being a parent? You want a ‘thank you’ for the shit fuckin’ job you did?”

“You’re in my house son, I deserve some goddamned respect!” Face contorting into an ugly veneer of rage, John hurled the whiskey glass across the room and into the darkness where it crashed loudly against the wall. 

“Really dad? That’s _real_ mature of you, throwin’ things across the room like a damn five-year old. Grow up!” Dean yelled, eyes wide.

“Don’t you talk down to me Dean! I am your father!” John screamed, punctuating that sentence by swiping the bottle of whiskey from the coffee table and hurling it at Dean’s head. The young man ducked, the glass shattering against the wall behind him violently, and upon straightening found John propelling himself towards him in a rage. He gave Dean little time, and swung a fist into the young man’s jaw fiercely, sending him staggering off to the side, the next punch swiftly burying itself into his stomach. Dean fell to his hands and knees and spluttered harshly, struggling after the wind was knocked from his lungs, the glass on the wooden floor slicing into his right hand deeply. Fuck, that was gonna be difficult to work with.

“Fuckin’ worthless brat!” His father spat out above him, and drove his boot into Dean’s ribcage. The boy cried out, crashing into the wall behind him before falling to his side, laying atop the shattered glass and spilled whiskey. He coughed and then groaned as pain shot sharply through his side. Could be a cracked rib or two. He’d probably have to get Bobby to check it.

John took the opportunity to stomp twice more upon Dean’s hip and thigh viciously before relenting; it was no fun kicking a dog when he was down. And although Dean was a fighter, someone who would never back down from a fight until forced to, tonight he was simply never given the chance to.

His father reeled back, and with surprise Dean saw tears glinting in his eyes. “I wish it was you,” He sobbed, grabbing his head by the fistful and rocking back and forth as he staggered backwards, falling into the armchair behind him. “I wish it wasn’t Mary. I wish it was you.” 

At least on that the two men could agree.

His father crying with his head buried in his hands, Dean gingerly lifted himself from the floor, wincing as the movement shot pain through him anew. Blood dribbled from a cut lip, tickling his chin, and his head pounded as he unsteadily stood. He braced himself against the wall, his hand leaving a crimson smear on the old wallpaper. He would have to clean that later lest he wished to repeat tonight’s incident.

Glass crunching under foot, Dean hobbled to his bedroom, his father’s sobs stalking his retreat until he had shut the door behind him with a soft click. He then bolted the door. 

It was quiet in Dean’s corner of the house save for the faraway hooting of an owl. Sammy would’ve loved that, owls were a special rarity in the outer Chicago suburbs. In a couple laborious steps, Dean crossed through the darkness and fell onto his bed with a grunt as he bounced on his ribs. Yeah, he was gonna need to check that. Reaching an arm to the side, Dean turned on the bedside lamp, before slowly raising himself like a zombie to sit on the edge of the mattress. He lifted his shirt and prodded gingerly at his side, fingers pressing against solid bone and lumpy skin. Nothing was broken but it hurt like a _bitch_ , more than previous experience with John’s boot. Dean worried his lower lip between his teeth. He definitely needed to get Bobby to check it. Or maybe he could just leave it, and possibly die. Yeah, that would be easier.

Speaking of. 

Dean swung between his legs to reach under the bed, and pulled out the old cookie tin he kept hidden away there. He placed the tin box on his lap, the weight of it settling heavily on his thighs, and absently ran a hand over the lid, smearing it with blood.

“Shit.” He muttered, turning his hand over and inspecting his palm. Luckily, the gash wasn’t too deep, and hopefully with a good bandage the hand would be fit for use with minimal problems. 

Dean clean the lid of the box with his sleeve and staunched the cut with a shirt he grabbed from the foot of his bed and turned his attention back to the scratched-up metal before him. It was a powerful box, the culmination of years of working hard, street racing, and squirrelling away every spare cent and penny that remained. It must’ve been the most expensive cookie tin in the world, as currently, it was worth some twenty thousand dollars. Dean fiddled with the lid, running his fingers over the cool cobalt metal. This box was destined for Sammy. It was the beginnings of a college fund, mighty enough to help send him to a new chapter in his life, to break him free of the social circumstances that were threatening to bind him. But it also held the power to save his father, Dean could be a good son, he could sacrifice this for the man that raised him. His fingers stilled over the worn image of a blue jay. John did this to himself. He didn’t deserve Dean’s help. Why did the thought even cross his mind?

Dean slept uneasily that night. He awoke before sunrise and lay in his bed, exhausted, watching the sky outside lazily transition from purple to orange to yellow to blue. There were birds chirping happily in the crisp air, heralding the new day and celebrating together having survived yet another freezing night. Dean looked over to the alarm clock besides his bed. 7:28. He needed to be at Bobby’s garage at eight.

Lifting himself from his warm cocoon with a groan, the boy dressed quickly from the floor, throwing last night’s whiskey-soaked shirt into a corner and hissing as pain blossomed brightly with every twist of his body. He donned his thick navy jacket and laced his boots before grabbing the tin box from under his bed and limping to the door. Dean steeled himself, before in one swift movement, unbolting the lock and opening it delicately.

The house was silent. For a moment Dean waited, his ears attentive for any sign of life from inside the glum building. The only sound came from the birds outside his window. The youth crept through the house, passing by the living room and finding his father passed out in the armchair, head lolling to the side and television still on, before swiftly gliding to the front door. He released a shaky exhale once he was outside, relief washing down his body, and headed to the Impala.

Winter was coming fast, the morning air everyday was biting sharper at bare skin and cunningly sneaking through layers of clothing. It stiffened his already stiff muscles. Very soon, Dean wouldn’t be surprised to walk out one morning to find snow dusting the ground delicately, and in a couple days he would need to make the effort to cover the cars at night or risk waking to find their windows frosted over. Dean jumped into the Impala and rubbed his frozen hands. Fingers stiff, he started the Chevy and blasted the air, gritting his teeth as he was hit with a wave of icy wind before slowly it began to warm up. 

Although he hated mornings, Dean did love driving in them, as the streets were near deserted and the sky was a soft pale blue, the sun softly illuminating the world in a mellow glow. It was peaceful, and gave him a weird sense of being the only person in the world. Complete and utter freedom to explore the beauty before him. It was strange that it didn’t fill him with a sense of loneliness.

He pulled into Bobby’s garage about five minutes late but knew that the man wouldn’t mind. The eight o’clock start was a thinly veiled ploy to ensure that Dean was there and ready at nine with a full belly to get him through the morning. Dean called it ‘babysitting’. Bobby called it ‘avoiding having his employees pass out on him and all the consequent hassles’.

Parking his car at the back of the garage, Dean swung open the door of the Impala, gritting his teeth as the frigid air flooded the car, and jumped out, tin box secured snugly under his arm. The muted sounds of classic rock drifted from within the garage and the scent of coffee mingled in the air with those of grease and gasoline. Dean smiled the tension loosened its grip on his body. The ideal way to start the morning.

Dean hobbled to the back door and with some effort let himself into the garage, closing the door firmly behind him to not permit the heat escape. The walls of the large workshop were lined with wrenches, hammers and spanners, cabinets sitting below and chains hanging above. The two large roller doors were shut against the cold and overhead swung light bulbs that lit the space with a warm yellow light. Bobby was buried under a cream-coloured pickup, the sounds of a ratchet clacking away rhythmically from underneath the truck.

“Mornin’ Bobby.” Dean needed to shout to be heard ZZ Top and their blues. He stalked over to the radio to turn down the volume a notch and the clacking stopped, followed by the sounds of Bobby rolling out from under the car soon after.

“You’re late, son.” He grumbled. He stayed atop the board for a short while, eyes darting across the bruise on Dean’s face before he lifted himself, lips pressing firmly into a line beneath his beard. He didn’t comment on it, over the years he had learnt not to in order to avoid putting Dean on the defensive, but that never stopped him from making his displeasure known through other ways.

Dean glanced at the clock on the wall. “Yeah, well, you’ve had the last ten minutes to get used to it.” He retorted and Bobby snorted. The older man sauntered towards him, wiping his hands on a towel tucked in at his belt. He wore his usual attire, jeans, plaid shirt, puffer vest and his signature trucker’s cap that served no purpose whatsoever in this weather. His grey eyes shifted to the tin under Dean’s arm and he gestured with his chin.

“What’s in the box?” He inquired. Gingerly, Dean took the tin from his armpit and held in between his hand with the same delicacy if he were holding a baby. The light from the hanging bulb glinted off the surface.

“Bobby, I gotta ask you somethin’.” 

For a moment Bobby stood silently, regarding Dean with a quiet expression. “Okay,” He had picked up on Dean’s tone, on the look in the boy’s eye, he knew him well enough to sense when Dean was about to bare his soul a little more than he would like to. They were rare moments. “This sounds like a conversation I need to be awake for.” He stated, heading off in the direction of the kitchen. Dean followed behind, hobbling as best he could on his stiff leg, and Bobby glanced back to ensure the boy was coming.

“Jesus shit boy, are you _limpin’?_ ” The words left him in a supressed fury and he slowed, Dean falling into step beside the older man.

“No.”

“You seriously comin’ to the garage in that condition, ya idjit, you’re in no condition to work.” There was no real heat behind the words, but the old man’s annoyance wasn’t feigned. The two dodged passed the pickup and wove around a couple trollies that had been pulled out from the wall. Dean merely shrugged in response. 

“I’ve managed worst.”

Bobby snorted. “Yeah, under ya own direction and no offense, but you’re a regular Dr Rumack.”

Dean rolled his eyes. “I’ll do some filin’ then.”

“You bet your ass you’re filin’ today.” Bobby grumbled, holding the workshop door open.

Along the eastern side of the garage sat a reception, a pair of offices and a small common room with a kitchenette, all fitted with large windows that let the golden morning sun shine through. They bee-lined to the latter room, the smell of fresh coffee filling the space with earthy aromas and alerting Dean’s brain to the presence of caffeine. Bobby already had a batch ready, and served them both mugs of the hot liquid whilst Dean sat himself at the round table. He placed the tin before him and contemplated the object, his ruminations interrupted by the other man placing a steaming mug before him.

“So, what is it that you wanna ask?” Bobby initiated, settling back in his own chair to consider the boy across from him evenly. 

Dean pushed the box towards him and sat up, leaning on the table. “I need you to look after this for me.”

Bobby’s eyes flicked to the tin again, and returned to Dean’s face, nervous. “What is it?”

“My life savin’s, can’t exactly keep it at home anymore.”

“Fair enough.” The older man took a sip from his mug, relaxing somewhat. Dean didn’t know how he could do that, sip scalding hot coffee. He played with his own cup, warming his hands on the ceramic and dragging his thumb across the lip deliberately.

“And uh, I need you to give it to Sam when he gets into college.” The boy added, timid.

“The fuck I will.”

“Bobby-” Bobby didn’t let Dean interrupt him, and ploughed over the boy’s objections, his tone stern and forthright.

“Sam’s already got a free ride on scholarships; you and I both know it. These are your savin’s you should be using at least some it on you, boy. And if you wanna give him some, you gotta give it to him yourself.” He waited expectantly for a response from Dean, who furrowed his brow irritably. 

“Just, promise me that if something happens to me-”  
“No, Dean. _You_ promise _me_ that you’re gonna be around to see him graduate.”

Dean couldn’t see the harm in lying. “I promise.” And it wasn’t wholly a lie. Dean wanted to be there when Sam graduated, and like hell he wasn’t going to try his hardest to watch his baby brother take his first steps into the world. But what he was really promising was to try. To try his best to be there. Bobby looked at him knowingly and nodded to himself.

“Good.” He stood and crossed the room to lay a hand on Dean’s shoulder briefly. “Nuke yourself some breakfast before you get started. And I’m gonna take a look at those bruises you’re hiding too, don’t think you’re so slick boy.”

_Novak_

Castiel felt as if he had effectively been sidelined by his own investigation. With Hell’s shut down for the short foreseeable future, the detective was without a CI and back to the more traditional and slow methods of investigation. The Demons too had been rather inactive lately, a fact that Captain Zachariah celebrated and attributed to Castiel’s ‘fantastic detective work’ although Castiel knew better. And besides, Zachariah was a glib moron, everyone in the precinct thought so.

The detective chose to spend his time doing surveillance. He reached out to enter into communication with the official taskforce for _sanguine_ but found their officers and intel to be of very little use. It almost seemed as the taskforce was selectively made up of the worst officers from each precinct, and lead by people who seemed rather disinterested in the whole affair. Castiel remembered begging to be assigned to them, but his attempts were rebutted as ‘his skills were too invaluable and needed here’. Castiel never believed that, not even for a second.

His car had become a temporary office, a place where he could sit in peace and in silence and not worry about wandering eyes whilst he searched through case files and drew up maps. Of course, there were certain luxuries the vehicle could not afford him. The federal database for one, and access to the evolving technologies which made his job easier, quicker. But when it came down to just needing a moment to think a problem through, to ponder and consider and speculate uninterrupted, the interior of the Ford would do just fine.

But that same Ford would not become his surveillance vehicle, for that he utilised an ’89 Mazda 323 which he’d bought from a guy needing to upgrade their family vehicle as baby number 2 was on the way. Castiel paid cash. 

Most nights, Castiel would follow known Demon routes, tracking identified members and marking those they interacted with. Over time he had built up his own database of people, places and things, an encyclopedia of all things Demon, but the more he unearthed about the gang, the more gaps he uncovered. Almost as if he were fumbling through the dark, trying to determine the shape of some unknown object only by touch and finding a myriad of crevices and holes. There was a piece missing, some critical information that would change the game. He was so close to finding it but never had felt so far from the truth. He had theories, of course, each a little crazy, but nothing substantial enough to justify pursuing their route.

Until then, Castiel’s best weapon would be his map. It was a unique map of Chicago in the sense that it was a comprehensive grid of trade routes, gang areas, fences, laundering points and possible drug laboratories. Most likely the most accurate chart of the city to date and not available in any giftshop. But currently, one particular point was of grand interest to the detective; a warehouse on the edge of the miserable suburb of Cicero.

Over the course of the past few weeks, Castiel had traced dealers and suppliers down to one building along the canal, and was positive that inside those dirty grey brick walls sat a _sanguine_ laboratory, or at least one of them. But it was Cicero’s proximity to Angel territory that was of immediate concern to the detective, as if Demon dealers decided to push a bit further and deal closer to the border, then retaliation in some form could be expected, followed by a hit on any number of possible locations and almost all certainly guaranteed to end with civilian casualties. And that was what Castiel wanted to avoid.

Unable to organise an operation and unable to trust the taskforce, Castiel did the one thing he could think of; go over his superior’s heads. And an anonymous tip to the FBI would be an effective way to do so. 

With several weeks of surveillance and enough evidence to assure him, Castiel headed to Cicero. The Mazda came to stop in the freezing air, a block away from the Demon’s warehouse, and from the car jump out the detective, wrapping a trench coat around himself and hiding his shirt, badge and gun, before striding to the payphone on a far corner, the glum grey building still in his sight. He dialled the FBI tip line.

The dirty glass box felt exposed, the streetlamp overhead illuminating the corner almost like a spot light. Holding the plastic phone to his ear, the detective glanced around the area. There was no one in sight and only few cars passed him by, seemingly as eager as he was to be out of the streets at this time. If only they knew just how close they were passing by to danger.

“FBI civilian hotline.” A lady’s voice crackled through the old speaker by the detective’s ear, returning his attention to the payphone.

“Ed Meyer road, Cicero.” He spoke lowly, curling around the plastic as if to protect it, his blue eyes searching through the darkness for trouble. Surely the Demon’s would have their own security milling around.

“Excuse me?” Came the voice again.

“There’s a warehouse surrounded by armed security, no uniforms, and unmarked trucks that go in and out of the grounds. They operate almost exclusively at night.”

The was a brief silence on the other end and Castiel glanced around furtively, spotting a man leaning against a building a way behind the detective, too far to be able to pick up on their conversation but close enough to be of suspicion. He was staring at the ground with a beanie covered head, his hands in his pockets, thinking.

“How long sir?” The voice returned. “Did you see this with your own eyes?”

Castiel turned back, keeping an eye on the building’s reflection in the scratched glass. It wasn’t clear.

“I started working nearby about a month ago,” Castiel lied. “I see them every time I drive home but they don’t try to make it obvious. Different vans.”

“And where did you say you were again?” The repeated question was the announcement that the detective was waiting to hear; that they were paying attention.

“Ed Meyer road, Cicero, Chicago.” He hung up. Something moved in the reflection, and Castiel spun to find the man still there, lifting his arms to light a cigarette, cupping the waning glow with gloved hands. The detective narrowed his eyes. The man was relaxed, nonplussed, and his thick coat covered any lumps or bulges that could elude to a weapon. It was best not to take unnecessary risks.

Trying not to seem too hurried, Castiel took off and crossed the street, heading back to where he had parked the Mazda in a brisk pace. He strained his ears, not picking up on any footsteps on the asphalt behind him, but again, that didn’t necessarily mean anything. The detective picked up his pace as he hopped onto the sidewalk on the other side of the street and continued alongside another tall building for a while, before finally coming across another intersection. He jumped off the curb with a diagonal path, so that through the reflection of the storefront windows he could see the opposite side of the street. They gave the detective a wide view of the empty street, the scene being presented to him almost like a painting; dark grey blocky buildings that imposed over the road, the empty asphalt marked with faded yellow lines, cones of lights falling from the towering streetlamps, and the detective in the midst of it all, trench coat billowing behind him, second shadow lurking around the corner.

Castiel buried his hands in his pockets, trying not to alert the other man that he had seen him, and hurried. The Mazda was parked only a short way away and only took seconds to reach, the man pulling out his keys and unlocking the driver’s side swiftly. He swung open the door, the window catching his tail’s reflection as the black-clad man began to run towards the detective, and jumped into the vehicle. Castiel wasted no time with starting the engine and floored the acceleration before he had even shut the door, taking off with a roar into the night. As the puff of pale exhaust dissipated into the air the detective turned his eyes to the rear-view mirror, the cloud parting to reveal the other man, who stood still in the middle of the street, silent, shrinking away until Castiel turned and he disappeared altogether from his sight.

_Winchester_

The re-opening of Hell’s was a rather grand affair.

A little bit of excitement did a lot to stimulate interest, and three weeks gone apparently called for at least three times the attendance. Tonight, the lot was swarming with people all eager to get their missing motor fix, including the Demons and even the Aberdeens amongst other members of Chicago’s underworld royalty. 

Inside the stuffy shed, Dean’s eyes flicked through the sign-up sheet for members to compete against. There was a Tom Brady, Meg Masters again, a few others that Dean didn’t recognise and Ruby, who had drawn the most sarcastic love heart besides her name. Ruby was a wildcard; she didn’t play by the rules, and was a real speed demon by the true sense of the word. If you wanted to beat her, you had to race at her level and not be afraid to play dirty, and that’s what made her the perfect in to the Demon gang.

He signed his name next to hers and Ash whistled as he watched on.

“Ya’know, the Chevy aint gonna come outta that one unscathed.” For a mullet-bearing redneck, Ash used a lot of words like ‘unscathed’ and ‘propensity’. Dean shrugged and tapped on the paper.

“Neither will Ruby.” 

Dean escaped from the marquee which was beginning to turn into a meat grinder and into the fresh crisp air, searching across the lot for his opponent and finding her by the edge of the track, lit by a flickering lamp. Ruby, the next big fish, was sitting disinterestedly against the hood of a red ’69 Dodge Challenger with black racing stripes running down the hood, an oldie but a goldie, and most likely heavily modded to hell. She was dressed in dark clothes to match her black hair, skinny jeans and thigh-high boots, and her hands rested in the pockets of her cropped leather jacket. A thick brow raised as Dean stalked towards her.

“Ready to get your ass kicked?” He teased, flashing her with a coy grin. Ruby, on her part, was unamused and wholly unaffected by the boy’s charms.

“Are you challenging me, Winchester?” She blew back, tone aloof.

Dean regarded her, tilting his head back as he did so. “Depends.” He leant forward. “Do all you Demons race the same?”

A huff. “Yeah, well, I’m not Meg.”

“No, Meg’s haircut is just-” With tight lips, Dean made a sweeping motion with his hand. “Terrible.” 

Ruby scoffed derisively and spun away from the boy to head towards the track. “I’ll see you on the starting line then.” She smirked, and stepped out from the spotlight.

Dean shoved his hands in his pockets and watched her go. He was jittery, buzzing in anticipation and anxiety and not just to get behind the wheel. There was a lot more resting upon this race, and this time he truly couldn’t afford to face the consequences of losing.

He headed back to take his usual place on the Chevy’s windscreen, relishing the heat that her hood emitted, but didn’t have to wait long before those grainy speakers barked out his name across the lot. He slid off the hood.

Dean rolled up to the starting point and came to a slow stop behind the red line, the Corvette purring excitedly beneath him. Besides the Chevy sat the Dodge, engine rumbling heavily and sending tremors through the asphalt, waiting for the moment when its prowess could be released in a glorious wild fury. Dean swallowed. The rumbling eluded to a deadly engine hidden under those racing stripes.

Ruby looked over at him from where she sat, a dangerous smirk tugging at her lips.

“Ready?” She asked. The boy nodded once and turned his attention back to the stretch of road before him. Onto the asphalt walked a guy that Dean didn’t recognise, clad in skinny jeans and a deep V-neck, a rocker looking type, and stopped between the cars with a familiar red scarf in hand. Ruby revved her engine, the sound ripping from the car in a deafening roar that shook every bone in Dean’s body. He glanced over at the brunette. She was smiling at him maliciously. Dean hated to admit it, but he was mildly terrified.

Suddenly, the red scarf came sailing down.

The two took off in an uproar of noise, wheels squealing as all of a sudden, the engines were pushed to their limits. Dean changed gears again and again as he gained speed, relieved to see that he had taken the immediate lead from the Challenger. But it didn’t last long, and as soon as the Chevy had settled into comfortably rapid pace, Ruby surpassed him. 

_Shit_. Shifting gear again, Dean all but sent his foot through the floor of the Corvette, trying to push his baby to the absolute edge.

“Come on, come on.” He breathed, the Corvette slowly managing to top her current speed. And then came the first corner. Dean’s saving grace was in fact the Challenger, as the ruby-red car had the same issue with weight as the Corvette did, and found itself sliding dangerously fast and far on the first turn. Ruby skidded wildly, the sounds of tires screeching filling the air as she sailed through the first turn, fishtailing wildly upon correction and losing speed due of it. Dean mostly followed suit, but corrected from the turn sooner than his opponent, minimising the fishtailing and allowing him more time to recover from the inevitable loss of speed. He caught up to the Dodge, the Chevy’s front wheels in line with the Challengers back ones, and sat there, riding Ruby’s blind spot.

If Dean managed to remain in position, the next turn would be in his favour. But clearly Ruby was aware of this too, as she sharply swerved, bumping into the Chevy’s side with a sickening squeal of metal on metal and forcing Dean to back off in a fit of unsavoury language.

“Son of a bitch!” He shouted as he jerked down on the steering wheel and shifted gears lest he stall. “That bitch!”

The second turn came and once again Ruby entered first, making little adjustment to her previous technique. Dean came out of the bend hot on Ruby’s tail, sitting only a bare few inches from the back of the Dodge and threatening to bump into the towbar. The avenue before them was rather long and well lit, drag conditions, and if the Chevy could get around the Challenger without Ruby knocking them into the curb, Dean could take a shaky lead.

Dean shifted gears and accelerated, moving out from his position behind the red vehicle and braving to creep up beside her. Ruby made her displeasure known, turning into Dean slowly and scraping up against the Corvette a second time.

“I’m sorry, Honey.” Dean breathed, keeping his foot firmly on the acceleration and daring to push back. He had a feeling that between the cars, the Chevy would be the lighter of the two. He just hoped he would figure that out before the vehicle and driver were pushed off the road and into the low fencing.

Teeth gritted and heart racing, Dean pressed forward, the Corvette managing to hold its own against the red racer. Slowly she crept up on the Dodge, but soon found herself inclining gently to the side. The scraping against the door reverberated throughout the car hollowly, and Dean almost slammed his foot on the brake in order to make it stop. The road began to widen underneath the two competitors, the two lanes splitting, and up ahead Dean spied his escape; concrete barricades that lined the island boundaries. He might have been in danger of being pushed to the side, but Ruby was in immediate danger of colliding head-on with the bollards. Through the driver’s window from the corner of his eye, Ruby whipped her head between him and the road, teeth gritted, before suddenly peeling off and veering to the other side, disappearing behind the streaks of grey. At the sudden loss of the Dodge on his flank, the Corvette suddenly twisted towards where the other car had been, and Dean frantically amended his steering to avoid following Ruby into the concrete barrier.

Finally free of his aggressor, Dean changed gears and accelerated again, striving to take the lead whilst the bollards provided him with protection. When the grey streaks fell away from his sight and the two lanes merged again, the Corvette had taken a small lead. There was another turn coming up, the exit route from the avenue, and Dean charged ahead to make the tight turn, unable to worry about the small overlap of the Challengers hood behind him. The exit crept up on them, a hairpin ben that neither of them would be able to take in their light cars without flying off the edge of it. Ruby slowed, but Dean didn’t relent, instead twisting the wheel sharply and spinning before he exited the avenue. He entered the turn at a 90-degree angle, skidding in sideways and accelerating once inside, wheels rapidly spinning in place dangerously close to the edge before finding ground and shooting off in a puff of smoke. He smirked as he took off down the new road, Ruby punching through the haze a few seconds after him. As long as he stayed out of her way, it was smooth sailing until they reached Hell’s. 

Ruby didn’t give up that easily. She was able to gain considerable ground with that powerful turbo engine that was borderline illegal and crept up on the Chevy throughout the remainder of the track. But it just wasn’t enough, and Dean entered the home stretch with more than a second between them.

He crossed the red line and the crowd erupted into a thunderous roar, a wave of awe and shock to find that it wasn’t the Dodge crossing that line first. It was Winchester, the underdog.

The Chevy headed to the edge of the track and Dean sat, both hands firmly on the wheel as he attempted to recover his breath and calm his fluttering nerves.

Holy hell. That was something else.

The Dodge spun past him in a blur of red, and headed towards the side of track that was always occupied by the Demons, the driver not sparing a glance in the Corvette’s direction. He winced as the light glinted off the scratches and gouges on the Dodge’s side, fully aware that the Chevy probably faired a lot worst.

“I’m so sorry, Honey.” He breathed. He owed the little Chevy a real long session in the workshop.

After a moments reprise, Dean shut down the engine and jumped out of the grey vehicle, shoving his hands deep in his pockets to hide that they were shaking and headed over to the trackside. The lot was absolutely crammed with people, and Dean had to push through the multitudes of denim and bare skin before he had made it to the other side of open asphalt. Overhead, the speakers turned on with a metallic whine and the names of the next racers were called out, the words almost lost to the constant murmuring of the excited people around him. Dean eyes travelled down the track, and at the end milled the Demons in their usual spot off to the side, gathered around beautifully kept muscle cars that glinted under the lamplight and chatting between them. Ruby’s beat-up Challenger sat at the edge, the driver standing a short way away and conversing with a few other Demon’s that Dean didn’t recognise. He sauntered over, their conversation pausing and heads turning wordlessly to face him as he approached. Ruby was the last to acknowledge him.

“You’re definitely no Meg.” The boy said in leu of a greeting. “That was a challenge.”

Slowly, Ruby turned, and looked him up and down pointedly before scowling. “If you came here to gloat, I don’t want to hear it.”

“Winchester.” Came a low voice from their sides. The group turned to find Azazel Aberdeen standing at the end of the Challenger, his strange yellow eyes gliding between them purposefully.

“I suppose a congratulations are in order now that you’ve taken down two of my finest.” He announced, shooting a pointed look at Ruby who glared in response. “I’d say that you’ve some Demon blood in you.” The sentiment was followed with a hollow laugh, and Dean suppressed a shiver. “Walk with me.” Azazel set off towards the lakeside and Dean followed.

“Winchester,” He began, yellow eyes glowing under the light. “You seem rather determined to make your way through my ranks.” A breeze passed through them and Dean shivered, pulling his jacket closer to him by the pockets.

“Just tryin’ to pay off a debt.” The boy explained. 

Azazel paused and turned to face the young man. “It wouldn’t be your father’s debt, perhaps?” He raised an eyebrow, quizzical and curious.

Dean’s eyes widened. “How did you-”

“Cause I’m the one he owes.” Yellow-eyes interrupted. He pursed his lips and huffed a short ironic laugh, adding softly with a flourish of his hands. “So that money you win from me just goes back to me.”

Dean scowled, skin crawling. It was a dirty feeling, the knowledge that the money paying for Sam’s law degree would be coming from winning against gang members in an illegal racing op. They came to a stop by the water’s edge and Dean looked out over the horizon, failing to find the point where the blue water stops and the black sky starts, the two great expanses melting into one another seamlessly.

Azazel looked amused.

“Look, kid, I can offer you a better deal. Work off your daddy’s debt with me, and when it’s repaid we’ll be even and you can go your separate way.” The Demon gazed at Dean whilst the latter chewed on his lip, looking down at the lights undulating reflection on the lakes surface, the white lines and dots trapped in perpetual motion.

“Doin’ what?” He inquired softly.

Azazel shrugged. “A little bit of this, a little bit of that.” He sung, nonchalant. “Mostly behind the wheel. Might need to use your charm once in a while. Stuff you can handle.” When no response came, the man added. “It’s your choice kid, you can decline if you want but I gotta warn you; daddy’s got a deadline.”

Dean’s gaze whipped back to Aberdeen and he stared at the man, stunned. 

“Your choice.” He reiterated flippantly. There was a distinct lack of emotion on his face.

The large expanse of sky began to fall down upon them. “When do I start?” The words rumbled in Dean’s chest. Azazel smiled, and clapped the boy on the back.  
“We’ll give you the proper welcome next week.” With a shrewd smile, Azazel stalked away, leaving Dean to stand alone by the lakes edge. 

Alone, Dean shifted on his feet and turned to contemplate that murky horizon. Looking out over the water, the darkness crept into his vision, swallowing the world and plunging it into darkness, narrowing it to only vague details and the sharp lines of the light’s reflection drowning at Dean’s feet. He searched out in the darkness, and found nothing twinkling in the distance.


End file.
